3-Hydroxybenzaldehyde → Methyl 4-((3-formylphenoxy)methyl)benzoate

HRID 520333Notes

Reaction equation

HRID 520333 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[O:24]>CC(C)=O>[CH:23]([C:22]1[CH:21]=[C:20]([CH:27]=[CH:26][CH:25]=1)[O:19][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:24]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 28825911Methyl 4-((3-formylphenoxy)methyl)benzoateYield 28%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A slurry of methyl 4-(bromomethyl)benzoate (1.4 g, 6.14 mmol), K2CO3 (1.02 g, 7.37 mmol), 3-hydroxybenzaldehyde (899 mg, 7.37 mmol) in acetone (20 mL) was stirred at room temperature for 16 hours. The solids were filtered, the filtrate partitioned between EtOAc (50 mL) and water (20 mL). The layers were separated and the aqueous phase back-extracted with EtOAc (3×30 mL) The combined organic phases were washed with brine (30 mL) and dried over MgSO4. The solvent was removed in vacuo and the residue was purified via silica gel chromatography (eluting with 0-20% isohexane/EtOAc) to give the title compound (464 mg, 28% yield) as a white solid.

Workup

  1. filtrationThe solids were filtered
  2. customthe filtrate partitioned between EtOAc (50 mL) and water (20 mL)
  3. customThe layers were separated
  4. extractionthe aqueous phase back-extracted with EtOAc (3×30 mL) The combined organic phases
  5. washwere washed with brine (30 mL)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified via silica gel chromatography (eluting with 0-20% isohexane/EtOAc)

Sources & evidence

ORD record
ord-b3766f5cce7c4825907d845767d121b4
Source dataset
uspto-grants-2016_05
Patent number
US09326976B2

Reaction notes

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